10 Small Towns in Connecticut You Might Fall in Love With


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Nowhere else in America has as many cute little towns as New England. Of all the states,  you’ll find some of the cutest small towns in the tiny state of Connecticut! In many of these towns, you are likely to explore destinations that embody pertinent historical landmarks and local traditions happening every year.

A white house in one of the small towns in Connecticut

From the cute coastal beach towns to the quaint historical villages, I’ll give you the inside scoop on the cutest small towns in Connecticut that you’ll love visiting.

Essex

Picture of an antique car in front of a white house with american flag bunting

A mention of Essex, CT, is the only way to start a list of the cutest small towns in CT. You’ll soon realize why it was voted one of the “best small towns in America.” The small-town charm captivates all who visit to experience a historic riverside town.

Essex is located in Middlesex County, right on the Connecticut River. The river played a huge role in developing the town. It’s famous for shipbuilding that you can learn more about in the Connecticut River Museum. The museum holds maritime exhibitions, shipbuilding artifacts, and, of course, gorgeous views of the river.

One of the best ways to take in the sights of the cute town is by cruise. The Essex Steam Train and Riverboat company is a popular tourist attraction giving leisure cruises in the Connecticut River on a historic riverboat. What a way to connect with the town’s past!

After spending time on the waterfront, head downtown and go for a stroll on Main Street. You’ll find lots of cute boutique shops and restaurants established in historic, federal-style buildings. You’ll find some of the best chocolate and truffles in the entire state.

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Chester

a classic new england white church with a tall steeple and snow on the ground

Nestled inside the Connecticut River Valley, the town of Chester will quickly become your favorite. Whether driving into town through the lush forest region or cruising in on the Chester/Hadlyme Ferry, you’ll be blown away by its charm the moment you lay eyes on it.

Chester is a historic town, first settled in 1692. With many historic buildings remaining, it looks exactly how you’d imagine an old town in New England. The quiet atmosphere and friendly people make it a relaxing place to visit.

Explore town to experience all that it has to offer – from history to culture. You’ll find many buildings listed on the National Register of Historic Places, including the Old Town Hall for its significance and private residences showcasing stunning architecture.

Hand around Main Street to find quaint boutique shops to explore or dine at award-winning restaurants. Many of the businesses are in preserved 19th Century buildings.

Small towns in Connecticut like Chester are popular for arts. There are plenty of art galleries around town showcasing local art talent. And if you’re lucky, you’ll get to attend a live performance showing at the Norma Terris Theater, part of Goodspeed Musicals.

Kent

A picture of a white house with red shutters behind a stone wall and a maple tree with yellow leaves

 Many people consider Kent to be an escape from the big city. With just a short train ride from New York City, the bustling metropolis views will quickly transform into lavish natural scenery. The cute town of Kent not only has visual appeal but there are plenty of fun things to do around town.

Kent is located right along the Connecticut – New York border. It gives a huge contrast to the big city because it’s known for its vast natural landscapes surrounding it. Kent Falls State Park is one of the most popular attractions for people visiting the town. The park is home to 17 waterfalls, including the largest in the state. It’s a fun outdoor destination for hiking and sightseeing.

Just like the other Connecticut villages and towns on this list, there are plenty of landmarks in Kent that you don’t want to miss. Have your camera ready as you approach Bull’s Bridge, one of three remaining covered bridges in Connecticut. If you’re a literary fan, you’ll have lots of great reading options in the House of Books and Kent Memorial Library.

Immerse yourself into the friendly community by stopping by the Kent Farmers Market to chat with the locals and shop for fresh produce.

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Mystic

A picture of a classic fishing boat against a dock in connecticut

If the name itself doesn’t pique your interest, Mystic will invariably encapsulate an ideal picture of a New England small town. In fact, it ranks as one of the best places to live with lots of people moving in from out of town. It’s one of those places that you don’t want to leave after experiencing how charming it is.

Mystic was once one of the most important seaports in Connecticut. Much of the maritime history is preserved in the Mystic Seaport Museum. Exhibitions detail lots of information about its history. And just outside the building are several preserved ship museums, many of which are listed on the National Register of Historic Places.

In a port that built hundreds of ships, you’ll still find boats floating around the harbor awaiting new passengers. Go for a cruise on a historic sailboat or steamship and have unbelievable views of the town’s waterfront against the lush trees in the backdrop.

You might even recognize a few places like the Mystic Pizza shop, which was featured in a major film. And if you like marine life, the Mystic Aquarium is one of the best in New England and home to majestic beluga whales.

Madison

a dark purple sunset or possible storm cloud hovers over coastal houses by the shore of CT

Madison is one of the larger towns on this list, with over 18,000 people living there. But what will really blow your mind is that every year, it receives over one million visitors – a majority arriving during the peak summer season. If you couldn’t figure it out by now, Madison is a cute town with picturesque beaches lining the entire shoreline.

Madison is located on the shore of the Long Island Sound. One of the main attractions is Hammonasset Beach State Park. Of all the big and small towns throughout Connecticut, Madison has the biggest beach, extending for two miles. So even with all the tourist traffic, there’s still plenty of room to sunbathe on the golden sands and go for a refreshing swim in the pristine blue waters.

There’s nothing better than taking a stroll through town to admire all of the cute New England-style buildings. There are several cultural venues highlighting art, music, performance, and more. The shops and galleries are excellent places to see the work of local artisans. And some fantastic shows and events happen at the Madison Arts Barn and Madison Art Cinemas all year long.

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Old Saybrook

A picture of an early morning along a new england waterfront, docks are empty

It’s hard to say whether Old Saybrook was as stunning in the past as it is today, but there’s something about the old town charm and landmarks that make it one of the prettiest places to visit in Connecticut today.

Old Saybrook was settled in 1635, making it one of Connecticut’s oldest towns. It’s strategically positioned at the mouth of the Connecticut River as it flows into the Long Island Sound. The position was an ideal location for Fort Saybrook, which now operates as a monument park.

Saybrook has the cutest lighthouse called the Breakwater Light. I recommend visiting during the evening to see one of the prettiest sunsets you’ve ever seen. The picturesque scenery could easily become your next postcard.

Old Saybrook has a couple of beach options like Harveys Beach and Indiantown Beach. A few steps from the coast and you’ll be in the heart of town. Beautiful colonial-era buildings line the small streets as you make your way to popular attractions like the Katherine Hepburn Cultural Arts Center. Dubbed ‘The Kate,’ the former town hall building now served as a performance venue for concerts and recitals.

Glastonbury

a brown building in a park with 4 empty wooden picnic benches out front on the lawn

If a cute town is what you’re seeking in Connecticut, look no further than Glastonbury. Not only is it a charming town in the present day, but it’s one of the oldest settlements in the United States. Perhaps its appeal is what keeps it around for so long.

A simple stroll around town will reveal why I had to include it on this list. And be sure to have your camera handy because there are tons of gorgeous architectural structures worth stopping to admire.

 Of all the small towns of Connecticut, Glastonbury has some of the most striking colonial-style houses. There are over 150 homes, some dating back as far as the 1600s. You’ll discover some of the oldest houses in the country. You can see other unique structures like the beautiful First Church of Christ. The town is a slice of New England heaven!

Don’t rush out of town too soon. Glastonbury is also known for hosting incredible events throughout the year. It’s a great way to mingle with the locals and enjoy some of the longstanding traditions. The famous Apple Fest happens in autumn with the apple harvest. Also, the Glastonbury Art Walk exhibits public art installations all around town for a blend of culture and history.

Putnam

A picture of a church and small town amidst greenery and a river

Visit Putnam in any season, and you’ll be amazed at how beautiful the town is. It’s located in the state’s northeastern region, surrounded by scenic nature. From the lush greenery in the summer to the colorful fall foliage in the fall, take a trip upstate to visit one of Connecticut’s cutest small towns.

Putnam is located along the Quinebaug River. The river is just one of the many natural landmarks. It’s surrounded by extensive forested areas where you can enjoy lots of outdoor recreation—one of the top destinations is the Putnam River Trail. Hiking, biking, and swimming are just a few of the recreational activities you can enjoy. And it’s also pet-friendly!

There are also tons of things to do in town. The pretty town is full of art and culture. You can check out popular venues like the Bradley Playhouse and the Complex Performing and Creative Arts Centre for live shows year-round.

Just like any other Small Towns in Connecticut, Putnam too has exciting festivals that happen annually. Head to Main Street for the car cruise or stick around for the light parade during the holidays.

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Cornwall

a classic bright red covered bridge in the autumn

The Small Towns in Connecticut cannot get smaller than Cornwall. The tiny town has just over one thousand people living there. It’s a friendly little place with a rural community and the cherished covered bridge landmark. What can be cuter than that?

Cornwall is a former farming town that had a brief moment of manufacturing. Now, it reverted to its roots and remains a quaint little town that’s self-sustainable. It has three main districts, each with its own characteristics. The favorite areas are the West Cornwall commercial district and Cornwall Village.

The most popular attraction in town is the Cornwall Bridge. This cute bridge is also one of the last remaining covered bridges in the state. It was built in the mid-1700s and is still used today. However, most people check it out for photos against the landscape backdrop.

During your visit, you’ll have fun recreational activities available on the Housatonic River. It’s popular for kayaking, canoeing, fishing, and camping. The locals are always hanging out, especially during the warmer seasons.

Stop by West Cornwall to browse the quaint shops full of cute souvenirs or diners serving delicious New England cuisine.

Milford

A picture of a snow-clad church behind a small waterfall dam in new england

Milford is one of the cutest small coastal towns in Connecticut. If it feels like you’re walking around an early English settlement, it’s because it’s one of the oldest towns in the state, with many buildings preserved since they were built. While it’s hard to narrow down some of the cool things to do in Milford, there are indeed things that you don’t want to miss.

Milford has a shoreline extending approximately 17-miles. Beaches line the entire coast along the Long Island Sound. An insider tip: Silver Sands State Park has the best beaches in town that I’m sure you’ll love! It also has the longest boardwalk. The beaches are perfect for sunbathing, swimming, and fishing. If you need a break from the water, head downtown and pop into one of the cute ice cream shops. Grab a few scoops and stroll around town to enjoy the charming New England vibes.

A couple of the must-visit attractions are the Audubon Coastal Center to see all the pretty birds from the observation deck or a quirky site like the PEZ museum. Take advantage of the Milford Welcome Center to find out everything happening around town.


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